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Transition metal-catalyzed process for preparing N-aryl amine compounds

a metal catalyzed process and naryl amine technology, applied in the preparation of amino compounds, organic chemistry, carboxylic acid nitrile, etc., can solve the problems of inefficient or economically unattractive methods for producing naryl amines

Inactive Publication Date: 2001-05-22
MITSUBISHI RAYON CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, to date, methods of producing N-aryl amines are inefficient or economically unattractive.

Method used

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  • Transition metal-catalyzed process for preparing N-aryl amine compounds
  • Transition metal-catalyzed process for preparing N-aryl amine compounds
  • Transition metal-catalyzed process for preparing N-aryl amine compounds

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Embodiment Construction

1-19

The known ligand DB.sup.t PF (1,1'-bis-(di-t-butylphosphino)ferrocene, Ligand 1) was evaluated in the amination reactions. DB.sup.t PF is air sensitive over long periods of time in solution, but can be handled and weighed in air. Table 1 summarizes the results with this ligand and others discussed below in the general reaction presented in Scheme I. In Table 1, yields are for pure isolated product and are an average of 2 runs on a 1 mmol scale using 0.5-1.0M concentrations, except for entry 15 (0.1 mmol scale).

The results of the amination reactions illustrate (1) remarkable rate enhancements for reactions with sterically hindered alkylphosphine ligands, (2) mild conditions for aminations of aryl chlorides, (3) amination of aryl tosylates, and (4) preparation of mixed alky arylamines in high yields by the metal-catalyzed amination of unactivated aryl chlorides with primary alkylamines.

DB.sup.t PF leads to exceptionally high-yield amination of activated aryl chlorides with aniline...

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Abstract

The present invention is directed to a process for the preparation of N-aryl amine compounds. The process of the present invention involves reacting a compound having an amino group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an N-aryl amine compound, the transition metal catalyst comprising a Group 8 metal and at least one chelating ligand selected from the group consisting of bisphosphines having at least one stearically hindered alkyl substituent. The formed products are valuable intermediates in the pharmaceutical and polymer fields.

Description

DESCRIPTION OF THE RELATED ARTN-Aryl amines compounds are important substructures in natural products and industrial chemicals, such as pharmaceuticals, dyes, and agricultural products, and are useful for screening for pharmaceutical and biological activity and in the preparation of commercial polymers. It would be advantageous to prepare N-aryl amine compounds from arylating compounds such as aryl halides and / or aryl tosylates because aryl halides are generally inexpensive and readily available, while aryl tosylates are easily prepared from phenols. However, to date, methods of producing N-aryl amines are inefficient or economically unattractive. Many known processes that generate a aryl-nitrogen bond must be performed under harsh reaction conditions, or must employ activated substrates which are sometimes not available. Examples of procedures that generate aryl amine compounds include nucleophilic substitution of aryl precursors as exemplified by Hattori et al., Synthesis 1994, 19...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C209/00C07C209/10C07C253/00C07D295/155C07C253/30C07D295/00C07C211/00C07C211/48C07C211/55C07C255/00C07C255/58
CPCC07C209/10C07C253/30C07D295/155C07C211/48C07C211/55C07C255/58
Inventor HARTWIG, JOHN F.HAMANN, BLAKE C.
Owner MITSUBISHI RAYON CO LTD
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